alpha-halogenvinylketone



Patented se uz, 1939 UNITED STATES PATENT OFFICE sumac a-HAIDGENVINYIKETONE mum- Walter Metsger. cologne-Dents, and one Leverkusen-I. G. Wei-k, Germany Bayer, signers to I. G. Farbenindnstrie on-the-Main,

schalt, Frankfortar Aktiengesell- Germany No mam. Application August s. 1938, Serial In Germany AW 3, 1937 2 Claims. 260-63) 1 taken by cooling to avoid an'exc'essive rise of temperature. A temperature of about 30 C. may be given as upper limit. The simplest method of splitting of! water from the c-halogenketobutanol which is tormed'as. intermediate product 'conslsts in subjecting the reaction mixture to vapor distfllation, the a-halogenvinylmethylketone distilling over in term of a water insoluble oil. The a-halogenvinylmethylketones are capable of being polymerized even on standing. The 25 polymeric products are solid and nearly colorless.

Moreover, they. represent valuable intermediate.

poduets for various reactions. I

The following examples illustrate the present invention without, however restricting it thereto 30 the parts being by weight:

- 'Eramplel to parts of vinylmethylketone are emulsified in 1000 parts of water while thoroug ly. stirring,

whereupon there are introduced within one hour at 540 '71 parts of chlorine while coolingr A colorless and nearlyodorless solution is-thus formed containing at the bottom a small quantity of a heavy oil. This by-product represents c-pdichloroethylmethylketone' which boils at 57 at 14 mm. pressure. The a-chloroketobutanolis isolated by saturating the aqueous solution by means of sodium chloride and then extracting it with organic solvents. On distilling oil the solvent. the final product is obtained in form of ayellow sirupy mass in a yield oi. 115 parts. The a-OhlOlO- vinylmethylketone can be transformed into the said aqueous solution by distilling it with vapor, the a-chlorovinylmethylketone being converted into a yellow oil heavier than water. After separating the layers and drying the oil with calcium chloride the product can be purified by distillation under reduced pressure. The a-chlorovinylmethylketon e shows a very high tendency to polymerize; it boils at 22-30 under 13 mm. pressure. Example 2 Into 1000 parts of water there are introduced while thoroughly stirringand cooling duringdhours about '10 parts ofvinylmethylketone and 160 parts of bromine, the reaction temperature being kept during thistime at 10-15". Thereupon the reaction mixture is distillated by means oi! vapor. 105 parts or a light-yellow, heavy oil, the major part or which consists of a-bromovinylmeth'ylketone, can be separated from the distillate.

we claim: r

1. a-halogenvinylmethylketones wherein them.

halogen is a member of the group consisting of chlorine and bromine.

2. Polymeric c halogenvinylmethylketones wherein the halogen is a member of the group consisting ot chlorine and bromine.

LOTHAR WALTER MEIZGER. 0'1'1'0 BAYER. 

